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One Woman's Not-So-Easy (But Not Impossible) Journey to Tech

If you found yourself on this blog post, welcome! I am going to assume you are here because you are trying to look for tips on how to secure your first tech job because you are experiencing job hunting burnout. I will be talking about the different steps I took to secure my first tech job and what an arduous journey it was.

Just a disclaimer: This blog post isn't one-size-fits-all. Everyone's journey to their first role in tech is vastly different and I am not here to teach you the "right" way to do it.

Who am I?

I am Katie, a career-changer who recently transitioned to tech after realizing that what I had studied in college (and the path I was subsequently on) would lead to a very unfulfilling life. I was born in Los Angeles, but have lived in Honolulu, Hawaii for most of my life. I have also lived in Japan, San Francisco, and I am currently located in Portland.

Table of Contents:

How It Started

Using Twitter in Your Job Hunt

Expanding Your Community Offline

Lessons I Learned


How It Started

The Origin Story

In 2016 I decided that the limited industries in Hawaii were not for me, so I moved to San Francisco on a whim because a relative had introduced me to the idea of working for a startup instead of a large corporation (which I was currently doing). While working customer support at an e-commerce startup, I befriended two of the three software engineers. We would often go to get coffee together and while on our coffee runs, they would always encourage me to learn how to program. Based on our interactions, they told me that I would be great at the problem-solving aspect of being an engineer. I shrugged off their constant recommendation, saying variations of "I am not good at math" and "I am not smart enough." But here is when it finally clicked. They told me:

Learning how to program is more similar to learning a second language than doing math algorithms.

AHA! I have learned a second language and actually loved it. Now that they framed it like that, I decided to give it a shot and bought my first Udemy course (which was the popular course by Colt Steele) in June of 2017. The funny thing is, I had no idea what Udemy was, but one of my friends happened to work at Udemy as a copywriter and she had told me all about the courses they offered, which is what got me started in the first place.

Bootcamp Logistics

After finishing the course, I realized I had fallen in love with web development. I enjoyed it so much that I decided I wanted to pursue it as a career. I knew I wanted to do a bootcamp because I enjoy structured learning but there were a few issues:

  1. I had no money to pay for a bootcamp
  2. I was living in San Francisco and couldn't afford to take time off of work to study full-time

This is when I decided to move to Portland, Oregon. I had attended the University of Oregon for one year back in college and already knew I enjoyed the state of Oregon. I also knew that Portland had a small tech scene growing, so I decided to give it a shot. In Fall 2017, I moved to Portland and found this program through the state of Oregon called TechRise which is a program for folks between the ages of 18-29 to help them get started in tech. After getting accepted into the program, I knew I wanted to apply for their scholarship which helps pay for the cost of a bootcamp, they also provide you with a monthly transit pass while you are in the program. I submitted the lengthy scholarship application and got amazing news. I received the full $7,500 amount to pay for my bootcamp (Epicodus).

The bootcamp I chose started in January 2018 and ended in May 2018. The track focused on HTML/CSS/Javascript, Ruby, Angular 2, and Rails. I had a generally good experience, but bootcamp experiences vary. Even people within my cohort didn't enjoy the experience. The specific bootcamp I attended focuses on pair programming.

After finishing the bootcamp I did a 3-month internship at a relatively large company in Portland doing marketing automation, which was my attempt at merging my past interest (marketing) with my current interest(coding).
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Using Twitter in Your Job Hunt

Who To Follow and Finding Community

In February 2018, I joined Twitter after a friend told me that it's the platform where people in the tech industry hangout (virtually, of course). I had never used Twitter before and was super intimidated. I had a flashback to something my Marketing professor had said back in college:

There are two types of people who use Twitter: The people who are creating content that people want to see, or the people who only consume the content.

This had me freaked out. I was so new to the industry I didn't think I had anything to say that people would care about, but I didn't want to just lurk...I wanted to be involved with the community. For a month, I rarely used Twitter, because I had no idea what to do. Then someone opened up their DMs for an AMA (Ask Me Anything) related to tech. My friend urged me to message him, so I did.

"How do you establish/cultivate a following on Twitter within the Tech world? I’m in a coding bootcamp now and I want to start making those relationships with people but I don’t know where to start! Thank you!"

He gave me invaluable advice. He told me to find like-minded people in the community and engage with their tweets. He also told me to share what I learn via screenshots and gifs.

I took his advice to heart, and immediately followed accounts of organizations I was involved with in the local community. For example, Women Who Code: Portland and Portland Women In Tech. I did a little research on who is involved with those organizations and followed them. Then I would keep an eye on people they would interact with and followed those people too. Now that I had people I was following, I actually had things on my timeline to interact with. I started replying in threads and would retweet heavily. Slowly but surely, I started to find the Portland tech community on Twitter.

Share Your Journey

Once I finished my internship (around August 2018), I knew I wanted to start using Twitter more strategically so that it could aid in the job hunt. I noticed that to cast a wide net in the job search, I needed to create more value because the truth is, your job search tweet has a higher likelihood of gaining more traction if people know you and what your story is. This is when I started participating in #100DaysOfCode and began sharing my daily progress. Because my internship wasn't very technical, I had forgotten how to do a lot of things, so it felt as if I had to relearn from scratch. I posted a lot of screenshots and gifs.

I also began tweeting more about what I have been up to, my frustration with job hunting, burnout, and other things that early-career developers could relate to. I even gave a talk at a local meetup about dealing with failure.

If you are concerned about growing your community around you on Twitter as an early-career developer, I would highly recommend trying to be transparent about your successes and failures. Failure is a hard topic to talk about, but ultimately, everyone can relate to it.

Find Job Opportunities

If you are comfortable with putting yourself out there, tweeting that you are looking for opportunities is extremely useful. After a while, I stopped cold applying to places, I exclusively used leads from Twitter as a way to job hunt. While I am no expert, I have a few Dos and Don'ts of crafting a job search tweet.


  • Say a little bit about yourself
  • Specify what you are interested in, like mentorship
  • Specify the location where you are looking to work (even it's remote or "open to relocation")
  • Specify the technologies you are comfortable with
  • Make sure you have a portfolio or website that you are comfortable with people seeing


  • Avoid being OVERLY specific about what you want in a job (if you are early in your career), people might see it and assume that you won't be interested in their opportunity
  • Avoid words that might make people discount your experiences. For example, I choose to use terms like "early-career developer," "career-changer," etc. rather than words like "junior"

While this term is commonly used to describe developers with little professional experience, I find the term particularly demeaning. It is a loaded word and while it is commonly used in this industry, I feel like in the English language there is a connotation that comes with it. For me, it feels almost juvenile. As someone looking for my first role in tech (which is incredibly difficult), I didn't want to associate myself with ANY words that could possibly give someone a reason to subconsciously discount my experiences before meeting me.
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Expanding Your Community Offline

Local Community Events

Engaging with my local tech community was another great avenue to meet more people in the industry. I even started my own meetup while I was still in code school! I am not saying that you have to start your own meetup to get noticed (though, this has been a great asset in job hunting because it shows that I care about the local tech community). Simply attending events consistently is a great way to engage and meet more friends in the community. While there are a lot of different types of meetups, I would recommend starting off by going to a few different meetups in the beginning, but then dial back and only attend your favorites. The reason I say this is that I, personally, get burned out when I am attending a million meetups a month. I took that pressure off myself by picking and choosing based on the content of the meetup and also the people who attend.

Other than meetups, I would recommend participating in workshops and hackathons. I participated in a hackathon (without knowing anyone else attending) two months into my bootcamp and it was a great experience. Humblebrag: Our team ended up taking first! It was a great way to work together with developers of varying levels. If you think you aren't good enough or that you will hold your team back, GET THAT OUT OF YOUR HEAD. There are ways to contribute to a hackathon team without contributing code. For example, the engineers on my team wanted to use React which I had never worked with before, so instead of holding everyone back or have them teach me React over a weekend, I decided to work on the presentation of our demo to set us apart from other teams. This included making a static website to present our project instead of using a slideshow and making a promotional video as if our product was going to market. Don't discount your other skills. People are multi-faceted and it is limiting to think that the only thing you can contribute to a hackathon team is code.

Workshops are another great way to not only level up your skill but meet people. I have done a few workshops and the best thing I usually take away is making new friends. If you can't afford to attend a workshop, usually there will be scholarship options, or you could reach out to the organizer directly and ask.


In my year and a half of being in the tech community, I have attended three conferences:

  • Write, Speak, Code (domestic)
  • ACT-W Portland (local)
  • JSHeroes (international)

Because I am a super big extrovert, I love going to conferences. This is not for everyone. I love interacting with people offline and meeting people not only in the local community, but domestically, and internationally. If conferences intimidate you, try and plan to go with a buddy to a smaller scale conference. Also, always make sure that a conference has a code of conduct. This is very important because you know that the conference prioritizes attendee inclusivity and safety. If you can't afford to attend a conference, keep an eye out for "student" tickets, scholarships, or even early-bird tickets. Don't see anything on the website? You can always reach out to an organizer and ask.

If you are up to it, try speaking at a conference or a meetup! You don't have to be a seasoned developer to talk about something cool you are working on or something you learned. You can also do a talk that is about you and your journey, which takes off the pressure of 100% technical accuracy.

Online Friends Become Offline Friends

One thing I would conscientiously do was to find people who are further in their tech careers and seem to have a dedication to raising up people early in their tech careers, whether by saying explicitly that their DMs are open or that they create educational content. I would engage with them and felt comfortable asking questions. I started meeting up with some of these folks offline, which is a great way to solidify online friendships. I have made so many lifelong friends through Twitter. If you are planning on meeting up with people you only know online, just make sure you make smart and safe decisions.
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Lessons I Learned

Find Your Focus

One reason my job hunt took nearly a year was due to me not having focus because of imposter syndrome. I knew I wanted to be an engineer because those are the problems I enjoy solving but didn't feel like my coding ability was good enough to make it through interviews. This resulted in me bouncing around to different paths. I was applying and interviewing for product designer roles, technical account manager roles, product owner roles, etc. I was basically thinking I would use my coding ability as a bonus for the roles I was applying for. I did this game of unfocused job hunting until around February 2019. It was then that I realized my true interest lies in UX engineering. I was able to learn this by working through different courses and tutorials and realizing the elements of coding that I like and don't like, what I am good at and what I am bad at. I have no doubt that finding what I like and doubling down on those skills early in the job hunt would have saved me months of terrible job hunting pain.

Work on a Side Project

Disclaimer: this may be difficult if you are balancing an already busy schedule while job hunting

This seems to be something that a lot of people recommend doing, but can honestly be hit or miss. It is a good way to show proof of your skills without being employed. For me, when I worked on my side project, it was less about proving my technical capabilities, but more about other skills that I wanted to cultivate. For example, when I had started my side project, I wanted to be a product owner/manager. Skills I wanted to show I had were:

  • Managing a team
  • Working with a distributed team
  • Researching
  • Data analysis

I tackled all these by forming my A-Team, which consisted of a product designer (Honolulu), a frontend engineer (Chicago), and a backend engineer (Portland). Before starting the application I did research regarding the type of product I wanted to build, the current climate of the market, and competitors. Then once I had an idea of what I wanted to do, I interviewed around 6 people in 30-minute sessions. After that, I transcribed our conversations, put notable quotes in a spreadsheet, and color-coded the cells based on common terms that came up. I re-oriented and then worked with my team for about 4 months on this project.

Contribute to Open Source

Disclaimer: this may be difficult if you are balancing an already busy schedule while job hunting

If you have never worked in a collaborative environment (one that involves doing a lot of merging, pulling, code reviewing, etc.) making contributions to open source can be a great way to get that experience. Finding beginner-friendly projects that have tags like "good first issue" would be a good place to start. Fixing documentation is probably the most approachable issue. In some cases, maintainers of the project are open to pair programming or helping you over their Slack channel if you get stuck or have trouble opening a PR. This not only gives you experience with git, but it also expands your network (noticing a trend in this post?), and it shows potential employers that you enjoy giving back to the community. When you get comfortable, tackle issues that are specific to what you want to learn, not necessarily what you are already a pro in. This gives you the opportunity to level up your skills in a low-pressure environment. Remember how I recommended that you should find your focus? Open source is a great way to try different types of things to see what you enjoy doing!

Give Back

If you have noticed a trend in this post, it's that I would be in a completely different place if it weren't for my community supporting me. This is why it is extremely important to give back when you can. We work in an incredibly collaborative industry. If someone helps you, try to pay it forward when you are able to. This doesn't mean that you have to become a mentor, create content, or donate a bunch of money. There are so many ways you can give back to the community, even sharing your journey to help others along the way is giving back!
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If you are to take away anything from this post it's that:

  1. Every journey is different so take everything with a grain of salt
  2. Community is everything, they will celebrate with you during the good times and support you during the hard times
  3. Doing things outside of just practicing whiteboarding exercises and studying algorithms is super important (in fact, I have never even looked at whiteboarding problems or common algorithms)


Try your hardest and don't let failure (or the fear of it) prevent you from reaching your goals. You got this!

Top comments (8)

vuild profile image

Congrats, you seem to be flying.


Takeaway #3, spot on. Make things.

avasconcelos114 profile image
Andre Vasconcelos

I feel like I have the opposite problem of Takeaway #3.

All I ever did was learn how to build things (self-taught programmer), and while I am somewhat confident in making things work, I have little to no clue of how to solve certain algorithms and most definitely never did any whiteboarding exercises

So I made it a personal goal for this year to go over at least a third of the challenges in leetcode, so I can get a good handle on how to pass technical interviews

vuild profile image

The opposite is not actually a problem but solid foundational basic knowledge can help experts too.


melissa profile image
Meli • Edited

Thank you for sharing your story and advice, Katie! I also come from a marketing background and would love to learn more about your day to day. I completely agree that joining a community of like-minded people can make a difference in your journey to tech.

ben profile image
Ben Halpern

Amazing read!

theisomorphic profile image

Wooo! ✌️ Great read :)

josef profile image
Josef Aidt

Great stuff, Katie! Keep it up!

flrnd profile image
Florian Rand • Edited

Failure can be a very good teacher too =). Well, I wish you the best of luck! But something tells me that you're not going to need luck ;) (Hard work will pay off)